(2S)-1,2-epoxyhexadecane | 82722-22-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (2S)-1,2-epoxyhexadecane
• 英文别名: (2S)-2-tetradecyloxirane；(S)-2-Tetradecyloxirane
• CAS: 82722-22-3
• 化学式: C₁₆H₃₂O
• 分子量: 240.429
• InChiKey: DSZTYVZOIUIIGA-INIZCTEOSA-N

物化性质

• 沸点：
  323.5±0.0 °C(Predicted)
• 密度：
  0.858±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  17
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2S)-1,2-epoxyhexadecane 在 Dowex 50W X₈ resin 、 sodium hydride 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (2R,2'S)-1'-O-(2'-hydroxyhexadecyl)glycerol
  参考文献：
  名称：

  （2R，2'S）-1-O-（2'-羟基十六烷基）甘油及其oxo类似物的高效立体选择性合成：鲨鱼肝油中潜在的抗肿瘤化合物

  摘要：

  已经描述了从鲨鱼肝油分离的标题化合物3的可再现的，高产率的，成本有效的，区域和立体选择性的合成。通过使4与C-13维蒂希盐顺序反应，由手性合成子4以41％的总收率制备化合物3。氢化; 环氧化和区域选择性开放。氧代类似物18和19是由四种不同的非手性合成子通过用不同的醇顺序地区域选择性打开相应的环氧化物，甲基化和脱保护策略而制备的。

  DOI：

  10.1016/0040-4020(96)00278-5
• 作为产物：
  描述：

  (2S,3Z)-hexadec-3-ene-1,2-diol acetonide 在 palladium on activated charcoal 吡啶 、 氢氧化钾 、 氢气 作用下， 以 甲醇 、 苯 为溶剂， 25.0 ℃ 、13.79 kPa 条件下， 反应 19.33h， 生成 (2S)-1,2-epoxyhexadecane
  参考文献：
  名称：

  （2R，2'S）-1-O-（2'-羟基十六烷基）甘油及其oxo类似物的高效立体选择性合成：鲨鱼肝油中潜在的抗肿瘤化合物

  摘要：

  已经描述了从鲨鱼肝油分离的标题化合物3的可再现的，高产率的，成本有效的，区域和立体选择性的合成。通过使4与C-13维蒂希盐顺序反应，由手性合成子4以41％的总收率制备化合物3。氢化; 环氧化和区域选择性开放。氧代类似物18和19是由四种不同的非手性合成子通过用不同的醇顺序地区域选择性打开相应的环氧化物，甲基化和脱保护策略而制备的。

  DOI：

  10.1016/0040-4020(96)00278-5

文献信息

• AMINOALCOHOL LIPIDOIDS AND USES THEREOF
  申请人：Mahon Kerry Peter

  公开号：US20110293703A1

  公开（公告）日：2011-12-01

  Aminoalcohol lipidoids are prepared by reacting an amine with an epoxide-terminated compound are described. Methods of preparing aminoalcohol lipidoids from commercially available starting materials are also provided. Aminoalcohol lipidoids may be prepared from racemic or stereochemically pure epoxides. Aminoalcohol lipidoids or salts forms thereof are preferably biodegradable and biocompatible and may be used in a variety of drug delivery systems. Given the amino moiety of these aminoalcohol lipidoid compounds, they are particularly suited for the delivery of polynucleotides. Complexes, micelles, liposomes or particles containing the inventive lipidoids and polynucleotide have been prepared. The inventive lipidoids may also be used in preparing microparticles for drug delivery. They are particularly useful in delivering labile agents given their ability to buffer the pH of their surroundings.

  本文描述了通过将胺与环氧末端化合物反应制备氨基醇脂质体的方法。还提供了从商业起始材料制备氨基醇脂质体的方法。氨基醇脂质体可以从外消旋或立体化学纯的环氧化合物制备。氨基醇脂质体或其盐形式最好是可生物降解和生物相容的，并可用于各种药物输送系统。鉴于这些氨基醇脂质体化合物的氨基基团，它们特别适用于多核苷酸的输送。已经制备了包含创新脂质体和多核苷酸的复合物、胶束、脂质体或粒子。创新脂质体也可以用于制备药物输送的微粒。鉴于它们能够缓冲其周围环境的pH值，它们在输送不稳定剂方面特别有用。
• Syntheses and interfacial behaviour of neoglycolipid analogues of glycosyl ceramides
  作者：Dominique Lafont、Marie-Noëlle Bouchu、Agnès Girard-Egrot、Paul Boullanger

  DOI：10.1016/s0008-6215(01)00255-5

  日期：2001.11

  Four glycosyl ceramides analogues having D-galactose or 2-acetamido-2-deoxy-D-glucose moieties linked to enantiomeric lipids have been synthesised to study their interfacial behaviour at the air \ water interface. The lipid chains were prepared in two steps by opening 1,2-epoxyhexadecane using Jacobsen kinetic hydrolytic resolution (KHR) followed by an azidosilylation reaction of the diol so obtained. Glycosylation reactions were realised either with 2,3,4,6-tetra-O-benzoyl-alpha -D-galactopyranosyl trichloroacetimidate or 1,3,4,6-tetra-O-acetyl-2-allyloxycarbonylamino-2-deoxy-beta -D-glucopyranose as donors and (2R)- or (2S)-2-azidohexadecanol derivatives as acceptors. Transformation of the azido glycosides into N-acylated products was done by a modified Staudinger reaction in the presence of fatty acyl chlorides. The four neoglycolipids are able to form a condensed monolayer at the air \ water interface; their pi -A isotherm diagrams are similar to that described for the natural glycosyl ceramides. The detailed analysis of the isotherms, taking into account the chirality of the lipid chains, allowed to determine the contribution of the different parts of the molecule under the monolayer packing. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Asymmetric synthesis of (+)-passifloricin A and its 6-epimer
  作者：S. Chandrasekhar、Ch. Rambabu、A. Syamprasad Reddy

  DOI：10.1016/j.tetlet.2008.05.070

  日期：2008.7

  Stereoselective total syntheses of the antiprotozoal natural product (+)-passifloricin A and its C-6 epimer have been achieved in similar to 5% overall yield. The strategy is based on Jacobsen epoxidation, Grubbs' metathesis and an Evans' intramolecular oxa-Michael reaction. (c) 2008 Elsevier Ltd. All rights reserved.
• A convenient resolution of long-chain alkyl epoxides with Jacobsen's salen(Co)III(OAc) catalysts
  作者：Prashant S Savle、Marika J Lamoreaux、John F Berry‡、Richard D Gandour

  DOI：10.1016/s0957-4166(98)00175-x

  日期：1998.6

  Non-racemic terminal long-chain alkyl epoxides are prepared from racemic epoxides and 1 mol% (R,R)- and (S,S)-salen(Co)III catalysts following a modified procedure for kinetic resolution. The ee's for all epoxides (C-10, C-12, C-14, C-16, C-18, C-20) exceed 95% and the chemical yields range from 85% to 95%. (C) 1998 Elsevier Science Ltd. All rights reserved.
• US8450298B2
  申请人：——

  公开号：US8450298B2

  公开（公告）日：2013-05-28